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Visible Light-Mediated Monofluoromethylation/Acylation of Olefins by Dual Organo-Catalysis.

Jiuli XiaYunliang GuoZhiguang LvJiaqiong SunGuangfan ZhengQian Zhang
Published in: Molecules (Basel, Switzerland) (2024)
Monofluoromethyl (CH 2 F) motifs exhibit unique bioactivities and are considered privileged units in drug discovery. The radical monofluoromethylative difunctionalization of alkenes stands out as an appealing approach to access CH 2 F-containing compounds. However, this strategy remains largely underdeveloped, particularly under metal-free conditions. In this study, we report on visible light-mediated three-component monofluoromethylation/acylation of styrene derivatives employing NHC and organic photocatalyst dual catalysis. A diverse array of α-aryl- β -monofluoromethyl ketones was successfully synthesized with excellent functional group tolerance and selectivity. The mild and metal-free CH 2 F radical generation strategy from NaSO 2 CFH 2 holds potential for further applications in fluoroalkyl radical chemistry.
Keyphrases
  • visible light
  • drug discovery
  • room temperature
  • high resolution
  • high throughput
  • risk assessment
  • single cell
  • mass spectrometry
  • highly efficient